CN104387270A - 1-isopropylcyclohexanol methyl propionate and preparation method thereof - Google Patents
1-isopropylcyclohexanol methyl propionate and preparation method thereof Download PDFInfo
- Publication number
- CN104387270A CN104387270A CN201410607992.4A CN201410607992A CN104387270A CN 104387270 A CN104387270 A CN 104387270A CN 201410607992 A CN201410607992 A CN 201410607992A CN 104387270 A CN104387270 A CN 104387270A
- Authority
- CN
- China
- Prior art keywords
- reaction
- isopropyl
- methylpropionate
- preparation
- cyclohexanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The invention provides a 1-isopropylcyclohexanol methyl propionate. The 1-isopropylcyclohexanol methyl propionate is characterized by being represented by the following structural formula as shown in the specification. A preparation method comprises the following steps of reacting cyclohexanone and a Grignard reagent to obtain 1-isopropylcyclohexanol and reacting 1-isopropylcyclohexanol and methacrylic anhydride to generate 1-isopropylcyclohexanol methyl propionate. By providing a compound and a synthetic route thereof and optimizing and screening the synthetic method, the problems of low yield, complex reaction and high purification difficultly are overcome and a product having the advantages of high yield, simple treatment process and high purity is obtained.
Description
Technical field
The present invention relates to a kind of synthetic method of organic compound, particularly 1-isopropyl cyclohexanol methylpropionate and preparation method thereof.
Background technology
Photoresist material, also known as photo-resist, refers to the irradiation by UV-light, electron beam, ionic fluid, X-ray etc. or radiation, the etch resistant thin-film material that its solubleness changes.What through exposure and development, solubleness is increased is positive photo glue, and what solubleness reduced is negative photoresist.By the difference of exposure light source and source of radiation, be divided into again ultraviolet photoresist (comprising the positive and negative type photoresist material of ultraviolet), deep ultraviolet light-sensitive lacquer, electron beam adhesive, X-ray glue, ionic fluid glue etc.
Photoresist material is the key material needed for production of integrated circuits, and it is with the development of unicircuit, constantly updates and regenerates.According to Moore's Law: the integrated level of unicircuit is doubled for every 18 months.This makes the processing live width of unicircuit constantly reduce, and improves constantly the requirement of photoresist material resolving power.Because the imaging resolution of photoresist material and exposure wavelength, exposure machine lens openings number are inversely proportional to, so shortening exposure wavelength is put forward high-resolution main path.
Up to the present optical lithography remains unchanged in occupation of dominant position in the production of super large-scale integration.Along with IC is to the fast development in submicron, deep-submicron direction, in photo-mask process, original lithography machine and the photoresist material that matches cannot meet the requirement of novel process.Therefore, deep research need must be carried out to photoresist material film forming material, sensitizer, additive, to adapt to the new requirement of photo-mask process.
The present invention studies discovery, and 1-isopropyl cyclohexanol methylpropionate is a kind of excellent electronic material, can for the manufacture of Other substrate materials.
But, more single limited for the manufacture of the material of photoresist material disclosed in prior art, and in synthesis technique, often there is purification difficult, side reaction is many, reaction yield is low, product purity is low, be not suitable for the problems such as large-scale industrial production.
Summary of the invention
The present invention is intended to overcome above-mentioned defect, provides a kind of new compound and synthetic route thereof, and is optimized screening to synthetic method, obtains a kind of productive rate high, and treatment process is simple, the product that purity is high.
The 1-isopropyl cyclohexanol methylpropionate that the invention provides, is characterized in that, shown in following structural formula:
In addition, present invention also offers the preparation method of above-mentioned 1-isopropyl cyclohexanol methylpropionate, it is characterized in that: generate 1-isopropyl cyclohexanol by pimelinketone and form reagent react; 1-isopropyl cyclohexanol methylpropionate is generated afterwards with methacrylic acid anhydride reactant.
Concrete synthetic route is as follows:
Concrete technology step is as follows:
Step one, protection gas environment under, in the solvent solution of MAGNESIUM METAL, drip 2 cbloropropane isopropyl chloride;
Wherein, the mol ratio of 2 cbloropropane isopropyl chloride and MAGNESIUM METAL is preferably 1:0.5-1.5.
Particularly, because Grignard reagent is easy to rotten, preferred field fabrication, reaction solvent of its reaction is selected from anhydrous solvent, any preferably in absolute ether, anhydrous THF and anhydrous methyl THF.
Its mass concentration of the solvent solution of MAGNESIUM METAL is 25-45%;
In step one, 2 cbloropropane isopropyl chloride is preferably dissolved in above-mentioned solvent and drips, and its mass concentration is 60-85%;
Above-mentioned 2 cbloropropane isopropyl chloride preferably drips in two stages; First stage, drip the 10-20% of 2 cbloropropane isopropyl chloride total amount under room temperature after, stop dripping, and by reaction being warming up to 50-60 DEG C of initiation reaction, now be attended by a large amount of exothermic phenomenon, stop heating, use water-bath cooling instead, after thermopositive reaction is stable, start the dropping process of subordinate phase, be added in reaction system by remaining 2 cbloropropane isopropyl chloride, the process of this dropping should keep reaction system to be in the state of micro-boil (67 DEG C-76 DEG C) all the time, and time for adding is about 1-3 hour.
In addition, in the process of above-mentioned steps one, initiation reaction can also be carried out by initiator.
This initiator amount is catalytic amount (0.01-2% of raw material total mass), can be used for the initiator causing grignard reaction for methyl iodide, iodine and glycol dibromide etc.
Under normal circumstances, the reaction of heating for some time is needed to cause during initiation reaction.If cause very slow, initiator can be added again.Once after reaction initiation, heat release can be very violent, at this moment need suitable water-bath cooling, ensure that reaction mixture refluxed steadily can not rush material.
Step 2, keep micro-state response 1-3 hour boiled;
This micro-temperature of reaction of boiling is about 67 DEG C-76 DEG C.Solution after having reacted is black gray expandable.
Step 3, reaction is cooled to less than 5 DEG C, drips pimelinketone;
The mol ratio of above-mentioned 2 cbloropropane isopropyl chloride and pimelinketone is 2.5-1.5:1.
Above-mentioned pimelinketone is preferably dissolved in above-mentioned solvent, and its mass concentration is 70-85%, and in the process dripped, its temperature should more than 5 DEG C, and time for adding is about 1-3 hour.
It is worthy of note, in the process of above-mentioned dropping pimelinketone, the very thickness that reaction solution can become, if increase the consumption of solvent (as: tetrahydrofuran (THF)), really can help to stir, but while cost significantly increases, the reaction environment crossed as dilution can cause the decline of productive rate.
Step 4, room temperature reaction 1-2 hour.
Step 5, reaction solution is poured in frozen water, after dripping acid solution, react 30-60 minute;
The amount pouring frozen water into is 10-40 times of pimelinketone input amount, and the acid solution of dropping is preferably concentrated hydrochloric acid, and addition is 2-10 times of pimelinketone input amount, and in the process of dropping, preferred control temperature is less than 20 DEG C.
Step 6, obtain 1-isopropyl cyclohexanol through aftertreatment;
In step 6, involved finishing sequence is the mixture doubly obtained in extraction liquid (as: methyl acetate, ethyl acetate, ether etc.) the extraction above-mentioned steps five of pimelinketone input amount with 10-15, merge organic phase, organic phase is doubly washed at least one times to 10% sodium sulfite solution of pimelinketone input amount with 3-15 again.Organic phase is concentrated, obtains product.Productive rate is 75-95%.
Step 7, protection gas environment under, system is cooled to less than-15 DEG C, adds organic bases;
Preferably be cooled to-25 DEG C to-15 DEG C.Any preferably in absolute ether, THF, anhydrous THF and anhydrous methyl THF of solvent in reaction flask.
Above-mentioned organic bases can be selected from the one in aminated compounds, the alkaline metal salt of alcohol, metal alkylide lithium compound, amido lithium compound.Most preferably be n-butyllithium solution (non-aqueous solution).
After adding organic bases, in the process dripped, should control to carry out when interior temperature is no more than-15 DEG C, add in about 15-60 minute.
Step 8, in reaction solution, drip 1-isopropyl cyclohexanol solution;
In above process, drip after preferably 1-isopropyl cyclohexanol being dissolved in solvent, its mass concentration is 40-60%; In the process dripped, in preferably controlling, temperature is no more than-20 DEG C, preferably in 30-90 minute, completes dropping.
Step 9, reaction is warming up to 20-25 DEG C, reaction 0.5-1.5 hour;
Step 10, cooling reaction, to less than 0 DEG C, drip methacrylic anhydride;
Preferably temperature is controlled within the scope of-5 to 0 DEG C, start to drip methacrylic anhydride, in this dropping process, preferably control to carry out when temperature is no more than 0 DEG C in it, preferably in 30-90 minute, complete dropping.
Wherein, 1-isopropyl cyclohexanol: organic bases: the mol ratio of methacrylic anhydride is 1:1-2:1-2;
The preparation method of methacrylic anhydride is: be that methacrylic acid and the methacrylic chloride of 1:0.5-1.5 reacts under the condition of strong base catalyst by mol ratio.
Particularly, this reaction is at room temperature carried out, preferred reaction solvent is chloroform, methylene dichloride, chlorobenzene etc., main reaction raw material is carried out mixture evenly after, drip triethylamine (mol ratio of triethylamine and methacrylic acid is 0.8-1.5:1), in preferably controlling in the process dripped, temperature is within 0 DEG C, preferably in 30-90 minute, completes dropping.
After completing above-mentioned dropping, poured into by reactant in frozen water, stir and leave standstill separatory, aqueous phase adopts chloroform, methylene dichloride, chlorobenzene equal solvent to extract, and merges all organic phases, after water repeatedly washs separatory, concentrates out desolventizing and be thick product.
In thick product, add the poly-resist (as: thiodiphenylamine etc.) being equivalent to product total mass 0.1-1% obtain highly purified methacrylic anhydride through underpressure distillation.
Above-mentioned poly-resist can be selected from phenolic inhibitor, quinones stopper, arene nitro compound stopper, mineral compound stopper.
Step 11, reaction is warming up to 20-25 DEG C, reaction 1.5-2.5 hour;
Step 12, obtain 1-isopropyl cyclohexanol methylpropionate through aftertreatment.
Aftertreatment in described step 12 is specially: poured into by reaction mixture in the frozen water and solvent that mass ratio is 2:1-2, stir after 30-60 minute, stratification, aqueous phase solvent extraction, organic phase successively with 10% sig water and water respectively wash at least one times, add desiccant dryness, after filtering siccative, filtrate carries out after adding the stopper of catalytic amount (0.1%-2% of product total mass) concentrated obtaining product; Its productive rate is about 70-85%.
Wherein, above-mentioned solvent is selected from the mixture of one or more in normal hexane, hexanaphthene, Skellysolve A, pentamethylene, normal butane.
Above-mentioned poly-resist can be selected from phenolic inhibitor, quinones stopper, arene nitro compound stopper, mineral compound stopper.
effect of the present invention
The present invention devises a kind of new compound, and 1-isopropyl cyclohexanol methylpropionate and a kind of new synthetic route are for the synthesis of 1-isopropyl cyclohexanol methylpropionate.Because the stability of this product is better, high temperature resistant, even distill for a long time, product also can not be polymerized, so can be widely used in various operating environment.
In the present invention, by generating 1-isopropyl cyclohexanol by pimelinketone and form reagent react; 1-isopropyl cyclohexanol methylpropionate is generated afterwards with methacrylic acid anhydride reactant.Its productive rate can reach more than 50%.
In the process of reaction, fresh few generation can produce dysgenic by product or other impurity to subsequent reactions, after each step completes, can be participated in next step reaction by simple aftertreatment, the basic needs that can realize suitability for industrialized production, its operating process is simple.
In addition, the precaution of each step of reaction of strict regulation are gone back in the present invention.As in step 3, be defined in dropping process in its temperature should more than 5 DEG C; Be defined in preferred control temperature in the process of dropping in step 5 and be less than 20 DEG C; Be defined in step 7 in the process of dropping, should control to carry out when interior temperature is no more than-15 DEG C; Be defined in temperature in preferably controlling in step 8 and be no more than-20 DEG C; Specify in step 10 temperature to be controlled, within the scope of-5 to 0 DEG C, start to drip methacrylic anhydride, in this dropping process, preferably control to carry out when temperature is no more than 0 DEG C in it.Also considered critical to obtain the approach of optimum yields.
In addition, also explicitly point out optimum response ratio and optimum response reagent in the present invention, as: the mol ratio of 2 cbloropropane isopropyl chloride and MAGNESIUM METAL is 1:0.5-1.5.The mol ratio of 2 cbloropropane isopropyl chloride and pimelinketone is 2.5-1.5:1.The mol ratio of described 1-isopropyl cyclohexanol and methacrylic anhydride is 1:1-2.
In addition, because the stability of this product is better, even distill for a long time, product also can not be polymerized, therefore, making of manufacturing, can by front-end volatiles after cut lower for purity and bottle residual collect together after reclaim product, thus improve the productive rate of product.
Therefore, the present invention by providing a kind of new compound and synthetic route thereof, and is optimized screening to synthetic method, overcomes that productive rate is low, reaction is complicated, purifying difficulty problem, and obtain a kind of productive rate high, treatment process is simple, the product that purity is high.
Embodiment
Embodiment one,
(1), reaction equation is as follows:
(2), concrete technology step:
Under nitrogen protection, be added in 738.7g tetrahydrofuran (THF) by 245g magnesium chips, add 1ml1,2-ethylene dibromide, stirs.Under room temperature, (30 degree) start tetrahydrofuran (THF) (1023.5g) solution dripping 2 cbloropropane isopropyl chloride (800g), after about dropping 10%, stop dripping 2 cbloropropane isopropyl chloride solution, and be heated to 60 degree, reaction causes gradually, at this moment a large amount of heat release, thermal source need be withdrawn, use water-bath cooling instead, after keeping exothermic heat of reaction stable, continue to drip (2 cbloropropane isopropyl chloride) monobromethane solution, remain micro-and boil (about 67 degree), within 1.5 hours, drip off, continue stirring after dripping off at this temperature and get final product (now solution is black gray expandable) in 2 hours.
Reaction solution is cooled to 0-5 degree, then drip tetrahydrofuran (THF) (636g) solution of pimelinketone (500g), control temperature is no more than 5 degree, within about 1 hour, drips off, after dripping off, then stirring at room temperature 1
ahour, sampling (middle control 1).Poured into while stirring by reaction solution in 10KG frozen water, slowly add 1.5kg concentrated hydrochloric acid, control temperature is less than 20 degree, adds rear continuation stirring 30 minutes,
Mixture uses 5400g extraction into ethyl acetate again, merges organic phase, and organic phase is again with 10% sodium sulfite solution washing (1500g × 2 time).Divide sub-cloud aqueous phase, upper organic phase is spin-dried for solvent (35 degree), obtains crude product 1209g (middle control 2), and underpressure distillation (oil pump, cut temperature 40-44 degree, oil temperature 70 degree) obtains product 513g (middle control 3)
(3), the treatment process of control in reaction:
(4), the screening of reaction conditions:
Embodiment two,
(1), reaction equation is as follows:
(2), concrete technology step:
1250g methacrylic acid and 1518g methacrylic chloride are added in 8379g methylene dichloride under room temperature, are cooled to-10-0 degree, drip 1575g triethylamine, warm <0 degree in controlling, drips off for about 45 minutes, sampling (middle control 1).Reaction mixture is poured in 10 kilograms of frozen water, stir stratification after 30 minutes, upper strata aqueous phase uses methylene dichloride (3990g × 1) to extract again, merge organic phase, organic phase washes with water again (2000g × 1), be spin-dried for solvent (30 degree), the crude product obtained adds the thiodiphenylamine of 1% (wt/wt) through underpressure distillation (oil pump, thorn type fractional column, cut temperature 75-80 degree, oil temperature 130 degree), obtain colourless liquid 1340g (middle control 2)
(3), the treatment process of control in reaction:
Embodiment three,
(1), reaction equation is as follows:
(2), concrete technology step:
Under nitrogen protection, be added in reaction flask by 712g tetrahydrofuran (THF), be cooled to-25--15 degree, then add 572g n-Butyl Lithium (density is the n-butyllithium solution of 0.65), in controlling, temperature is no more than-15 degree, within about 15 minutes, adds.Then after 216g1-isopropyl cyclohexanol being dissolved in 445g tetrahydrofuran (THF), slowly drop in reaction flask, in controlling, temperature is no more than-20 degree, within about 40 minutes, drips off.After dripping off, reaction flask is warming up to 20-25 degree and continues stirring 1 hour, is then again cooled to-5-0 degree, drops in reaction flask by 346g methacrylic anhydride, and in controlling, temperature is no more than 0 degree, within about 40 minutes, drips off.Remove ice bath, rise to room temperature (20-25 degree) and continue reaction 2 hours, sampling (middle control 1).
Reaction mixture is poured in 4000g frozen water and 2600g normal hexane, stir after 30 minutes, stratification, lower floor's aqueous phase uses n-hexane extraction (650g × 1) again, merge organic phase, organic phase uses 10% sodium hydroxide solution (150gNaOH+1350gH successively
2o) and water (1500g) respectively washing once, add 500g anhydrous sodium sulfate drying.After filtering siccative, after filtrate adds 3g thiodiphenylamine, decompression is spin-dried for solvent (35 degree), obtains crude product 519g.
Crude product obtains 237g product (middle control 2) through twice underpressure distillation (oil pump, thorn type fractional column collect 38-40 degree cut, oil temperature 100 degree).
(3), the treatment process of control in reaction:
(4), the screening of reaction conditions:
(5), spectrum analysis:
Molecular formula: C
13h
22o
2
m/z:210.16(100.0％)
Elemental Analysis:C,74.18；H,10.33；O,15.49
1H NMR(300MHz，CDCl
3)：δ6.065-6.063(d，1H)，5.496-5.488(t，1H)，2.747-2.678(m，1H)，2.257-2.229(d，2H)，1.940(s，3H)，1.681-1.169(m，8H)，0.885-0.868(d，6H)。
Claims (10)
1.1-isopropyl cyclohexanol methylpropionate, is characterized in that, shown in following structural formula:
2. the preparation method of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 1, is characterized in that: generate 1-isopropyl cyclohexanol by pimelinketone and form reagent react; 1-isopropyl cyclohexanol methylpropionate is generated afterwards with methacrylic acid anhydride reactant.
3. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 2, it is characterized in that, concrete technology step is as follows:
Step one, protection gas environment under, in the solvent solution of MAGNESIUM METAL, drip 2 cbloropropane isopropyl chloride;
Step 2, keep micro-state response 1-3 hour boiled;
Step 3, reaction is cooled to less than 5 DEG C, drips pimelinketone;
Step 4, room temperature reaction 1-2 hour;
Step 5, reaction solution is poured in frozen water, after dripping acid solution, react 30-60 minute;
Step 6, obtain 1-isopropyl cyclohexanol through aftertreatment;
Step 7, protection gas environment under, system is cooled to less than-15 DEG C, adds organic bases;
Step 8, in reaction solution, drip 1-isopropyl cyclohexanol solution;
Step 9, reaction is warming up to 20-25 DEG C, reaction 0.5-1.5 hour;
Step 10, cooling reaction, to less than 0 DEG C, drip methacrylic anhydride;
Step 11, reaction is warming up to 20-25 DEG C, reaction 1.5-2.5 hour;
Step 12, obtain 1-isopropyl cyclohexanol methylpropionate through aftertreatment.
4. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 3, is characterized in that:
The mol ratio of described 2 cbloropropane isopropyl chloride and MAGNESIUM METAL is 1:0.5-1.5.
5. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 3, is characterized in that:
The mol ratio of described 2 cbloropropane isopropyl chloride and pimelinketone is 2.5-1.5:1.
6. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 3, is characterized in that:
Described 1-isopropyl cyclohexanol: organic bases: the mol ratio of methacrylic anhydride is 1:1-2:1-2.
7. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 3, is characterized in that:
The preparation method of described methacrylic anhydride is: be that methacrylic acid and the methacrylic chloride of 1:0.5-1.5 reacts under the condition of strong base catalyst by mol ratio.
8. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 3, is characterized in that:
In step one, described 2 cbloropropane isopropyl chloride drips in two stages;
Wherein, the first stage, under room temperature, the 10-20% of 2 cbloropropane isopropyl chloride total amount is dripped;
By reaction being warming up to 50-60 DEG C of initiation reaction;
Subordinate phase, after thermopositive reaction is stable, is added into remaining 2 cbloropropane isopropyl chloride in reaction system.
9. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 3, is characterized in that:
In the process of described step one, initiation reaction can also be carried out by initiator.
10. the preparation method of a kind of 1-isopropyl cyclohexanol methylpropionate as claimed in claim 7, is characterized in that:
Aftertreatment in described step 12 is specially: poured into by reaction mixture in the frozen water and solvent that mass ratio is 2:1-2, stir after 30-60 minute, stratification, aqueous phase solvent extraction, organic phase successively with 10% sig water and water respectively wash at least one times, add desiccant dryness, after filtering siccative, filtrate carries out after adding the poly-resist of catalytic amount concentrated obtaining product;
Wherein, described solvent is selected from the mixture of one or more in normal hexane, hexanaphthene, Skellysolve A, pentamethylene, normal butane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410607992.4A CN104387270A (en) | 2014-10-31 | 2014-10-31 | 1-isopropylcyclohexanol methyl propionate and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410607992.4A CN104387270A (en) | 2014-10-31 | 2014-10-31 | 1-isopropylcyclohexanol methyl propionate and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104387270A true CN104387270A (en) | 2015-03-04 |
Family
ID=52605249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410607992.4A Pending CN104387270A (en) | 2014-10-31 | 2014-10-31 | 1-isopropylcyclohexanol methyl propionate and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104387270A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879756A (en) * | 2019-02-22 | 2019-06-14 | 江苏南大光电材料股份有限公司 | The preparation method of 1- isopropylcyclohexyl (methyl) acrylate |
| EP3524589A1 (en) * | 2018-02-09 | 2019-08-14 | 3M Innovative Properties Company | Process for the manufacturing of a (meth)acrylic anhydride in a flow reactor |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5461162A (en) * | 1994-07-27 | 1995-10-24 | Merck & Co., Inc. | Process of synthesizing n-acyl auxiliaries |
| JP2000319226A (en) * | 1999-05-07 | 2000-11-21 | Yasuhara Chemical Co Ltd | Preparation of tertiary alcohol organic carboxylate |
| JP2006104169A (en) * | 2004-10-08 | 2006-04-20 | Tosoh Corp | Method for producing tertiary cycloalkyl (meth)acrylate |
| US20070275324A1 (en) * | 2006-05-26 | 2007-11-29 | Robert David Allen | Low activation energy photoresist composition and process for its use |
| CN101277763A (en) * | 2005-09-01 | 2008-10-01 | 慕尼黑路德维格-马克西米利安斯大学 | Solutions of anhydrous lanthanide salts and its preparation |
| CN101930178A (en) * | 2009-06-24 | 2010-12-29 | 住友化学株式会社 | The manufacture method of chemical amplifying type photo-corrosion-resisting agent composition and corrosion-resisting pattern |
-
2014
- 2014-10-31 CN CN201410607992.4A patent/CN104387270A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5461162A (en) * | 1994-07-27 | 1995-10-24 | Merck & Co., Inc. | Process of synthesizing n-acyl auxiliaries |
| JP2000319226A (en) * | 1999-05-07 | 2000-11-21 | Yasuhara Chemical Co Ltd | Preparation of tertiary alcohol organic carboxylate |
| JP2006104169A (en) * | 2004-10-08 | 2006-04-20 | Tosoh Corp | Method for producing tertiary cycloalkyl (meth)acrylate |
| CN101277763A (en) * | 2005-09-01 | 2008-10-01 | 慕尼黑路德维格-马克西米利安斯大学 | Solutions of anhydrous lanthanide salts and its preparation |
| US20070275324A1 (en) * | 2006-05-26 | 2007-11-29 | Robert David Allen | Low activation energy photoresist composition and process for its use |
| CN101930178A (en) * | 2009-06-24 | 2010-12-29 | 住友化学株式会社 | The manufacture method of chemical amplifying type photo-corrosion-resisting agent composition and corrosion-resisting pattern |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3524589A1 (en) * | 2018-02-09 | 2019-08-14 | 3M Innovative Properties Company | Process for the manufacturing of a (meth)acrylic anhydride in a flow reactor |
| WO2019155385A1 (en) * | 2018-02-09 | 2019-08-15 | 3M Innovative Properties Company | Process for the manufacturing of a (meth)acrylic anhydride in a flow reactor |
| CN109879756A (en) * | 2019-02-22 | 2019-06-14 | 江苏南大光电材料股份有限公司 | The preparation method of 1- isopropylcyclohexyl (methyl) acrylate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2020113585A1 (en) | Acylphosphine oxide compound and preparation method therefor | |
| CN111138410A (en) | Acid-producing resin monomer for photoresist containing adamantane structure and synthetic method thereof | |
| CN104910012A (en) | Method for preparing 1-ethylcyclohexyl acrylate | |
| CN112679499A (en) | Sulfonium sulfonate photo-acid generator synthesized from matrine and synthesis method thereof | |
| CN104387270A (en) | 1-isopropylcyclohexanol methyl propionate and preparation method thereof | |
| CN111138287A (en) | Photoresist resin monomer synthesized from hexahydro-1H-indene-1, 3(2H) -diketone and synthetic method thereof | |
| CN104447311A (en) | 1-methyl-cyclopentanol-acrylate and preparation method thereof | |
| CN109879755A (en) | The preparation method of 1- ethylcyclohexyl (methyl) acrylate | |
| IT201800000667A1 (en) | PROCEDURE FOR THE PREPARATION OF DISPLACED DIARYLOXYHETERODIAZOLIC COMPOUNDS | |
| CN110698456A (en) | Synthesis method of 2, 3-dihydrothiochromen-4-one and derivatives thereof | |
| CN111548257B (en) | Preparation method of (4-isopropoxy-2-methyl) phenyl isopropyl ketone | |
| CN102295549B (en) | Benzindene triptycene and spirofluorene-benzindene triptycene derivative and preparation method thereof | |
| CN106905358B (en) | Preparation of vitamin D3Process for preparing analogue intermediates | |
| CN114315575A (en) | Preparation method and application of photoinitiator intermediate | |
| CN107602339B (en) | Method for synthesizing 4-hydroxymethyl biphenyl | |
| JP2002241363A (en) | Method for producing sulfonium salt | |
| CN112409176A (en) | Synthesis method of p-acetoxystyrene | |
| CN117003632A (en) | Method for preparing 5-bromo-4, 5-tetrafluorovaleric acid | |
| JP5681339B2 (en) | Method for producing compound | |
| JP5869664B2 (en) | Process for producing 5-oxo-4-oxa-5-homoadamantan-2-ol | |
| CN109305955B (en) | Preparation method of molecular glass photoresist containing tetraphenylthiophenol structure | |
| CN106977421A (en) | A kind of method for preparing diazo naphthoquinone type sensitising agent | |
| KR102226175B1 (en) | Method for preparing hydroxypyrene compound with high purity | |
| CN111875484B (en) | Continuous production process of metadiphenylacetone | |
| CN113105492B (en) | Preparation method of trifluoromethyl trimethylsilane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150304 |
|
| RJ01 | Rejection of invention patent application after publication |